I'm facing the same thing only they know me as Female Name and address me as she; my name change will be final next Tues. (I, too, am Jonathan!) and I plan on changing my ID. I'm not coming out at work until a) T has had more effects (I've been on it 8.5 weeks) and b) I have top surgery (Dec); and c) I'm sure my insurance has 100% paid for my hysto. They should, but I keep getting things in the mail that say total bill >$10K; we paid $1500, then another that says we paid $365, etc. Why they don't just pay the whole thing I have no clue. So I want that paid for before I tell work and have them switch my name/gender on the insurance.
I have a separate job with no insurance that I'll probably come out to as soon as my name has changed because there is no insurance involved and they never see me (online job).
Jay